Author/Authors :
Grant، نويسنده , , Andrew S. and Chaudhary، نويسنده , , Kleem and Stewart، نويسنده , , Lisa E. Peters، نويسنده , , Andrea and Delisle، نويسنده , , Spencer and Decken، نويسنده , , Andreas، نويسنده ,
Abstract :
A facile, racemic synthesis of a ‘twisted’ transition-state analogue of biotin is described. A key reaction is the electronically assisted ring-closure of the sulfur containing ring by displacement of an in situ generated mesylate by a suitably positioned 4-methoxybenzyl sulfide. The crystal structure of tricyclic compound 6 shows the AB ring system to indeed be twisted. The ‘twist’ was introduced to examine the possible involvement of sulfur participation in biotin biochemistry.
